Base Metal-Controlled Chemodivergent Cyclization of Propargylamines for the Atom-Economic Synthesis of Nitrogen Heterocycles

被引：1

作者：

Zhang, Hui ^{[1
]}

Zi, You ^{[1
]}

Cao, Chenhui ^{[2
]}

Huang, Weichun ^{[1
]}

Jiang, Aiwei ^{[1
]}

Lu, Chaowu ^{[1
]}

He, Jie ^{[1
]}

Tang, Yanfeng ^{[1
]}

Wu, Zheng-Guang ^{[1
]}

机构：

[1] Nantong Univ, Sch Chem & Chem Engn, Nantong 226019, Jiangsu, Peoples R China

[2] Anhui Sholon New Mat Technol Co Ltd, Chuzhou 239500, Anhui, Peoples R China

来源：

ORGANIC LETTERS | 2023年 / 25卷 / 50期

基金：

中国国家自然科学基金;

关键词：

2,3-DISUBSTITUTED INDOLES; CLAISEN REARRANGEMENT; DERIVATIVES; 2H-AZIRINES; ANNULATION; ALDEHYDES; ENAMINES; ANILINES; AMINES; ROUTE;

D O I：

10.1021/acs.orglett.3c03725

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Herein, a base metal-enabled chemodivergent cyclization of propargylamines for the atom-economic construction of nitrogen heterocycles has been developed. Due to the different modes of activation of metal to propargylamine, copper-catalyzed 6-endo-dig cyclization generates functionalized 2-substitued quinoline-4-carboxylates, while iron-promoted cascade amino Claisen rearrangement, aromatization, and aza-Michael addition afford diverse 2-substituted indole-3-carboxylate derivatives. Excellent selectivity, broad functional group tolerance, mild conditions, and flexible late-stage functionalization illustrate the high efficiency and synthetic utility of this chemodivergent reaction.

引用

页码：9030 / 9035

页数：6

共 31 条

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